- 18F-Fluorination of Unactivated C-H Bonds in Branched Aliphatic Amino Acids: Direct Synthesis of Oncological Positron Emission Tomography Imaging Agents
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A mild and selective photocatalytic C-H 18F-fluorination reaction has been developed that provides direct access to 18F-fluorinated amino acids. The biodistribution and uptake of three 18F-labeled leucine analogues via LAT1 mediated transport in several cancer cell lines is reported. Positron emission tomography imaging of mice bearing PC3 (prostate) or U87 (glioma) xenografts using 5-[18F]-fluorohomoleucine showed high tumor uptake and excellent tumor visualization, highlighting the utility of this strategy for rapid tracer discovery for oncology.
- Nodwell, Matthew B.,Yang, Hua,?olovi?, Milena,Yuan, Zheliang,Merkens, Helen,Martin, Rainer E.,Bénard, Fran?ois,Schaffer, Paul,Britton, Robert
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- N-sulfur aryl benzenesulfonyl imide and preparation method and application thereof
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The invention relates to N-thioaryl benzenesulfonyl imide and a preparation method and application thereof. The preparation method comprises the following steps: taking bis (benzenesulfonyl) imide asa raw material, reacting with sodium hydride to obtain a sodium salt of bis (benzenesulfonyl) imide, and reacting the prepared sodium salt of bis (benzenesulfonyl) imide with benzene (including substituted phenyl) sulfinyl chloride to obtain N-thioaryl benzenesulfonyl imide which can be applied to a thioarylation reaction. Compared with the prior art, the preparation method has the advantages thatthe reaction conditions are mild, the chemical yield is high, a new thioaryl reagent which is insensitive to water and air and relatively high in stability is synthesized, and the prepared N-thioarylbenzenesulfonimide can be used as an electrophilic thioarylation reagent with relatively high activity and has a very good application prospect.
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Paragraph 0031; 0034-0036; 0038-0040; 0042-0044; 0046-0047
(2020/11/12)
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- Site-Selective, Late-Stage C?H 18F-Fluorination on Unprotected Peptides for Positron Emission Tomography Imaging
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Peptides are often ideal ligands for diagnostic molecular imaging due to their ease of synthesis and tuneable targeting properties. However, labelling unmodified peptides with 18F for positron emission tomography (PET) imaging presents a number of challenges. Here we show the combination of photoactivated sodium decatungstate and [18F]-N-fluorobenzenesulfonimide effects site-selective 18F-fluorination at the branched position in leucine residues in unprotected and unaltered peptides. This streamlined process provides a means to directly convert native peptides into PET imaging agents under mild aqueous conditions, enabling rapid discovery and development of peptide-based molecular imaging tools.
- Yuan, Zheliang,Nodwell, Matthew B.,Yang, Hua,Malik, Noeen,Merkens, Helen,Bénard, Fran?ois,Martin, Rainer E.,Schaffer, Paul,Britton, Robert
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supporting information
p. 12733 - 12736
(2018/09/12)
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- Organomediated Enantioselective 18F Fluorination for PET Applications
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The first organomediated asymmetric 18F fluorination has been accomplished using a chiral imidazolidinone and [18F]N-fluorobenzenesulfonimide. The method provides access to enantioenriched 18F-labeled α-fluoroaldehydes (>90 % ee), which are versatile chiral 18F synthons for the synthesis of radiotracers. The utility of this process is demonstrated with the synthesis of the PET (positron emission tomography) tracer (2S,4S)-4-[18F]fluoroglutamic acid.
- Buckingham, Faye,Kirjavainen, Anna K.,Forsback, Sarita,Krzyczmonik, Anna,Keller, Thomas,Newington, Ian M.,Glaser, Matthias,Luthra, Sajinder K.,Solin, Olof,Gouverneur, Véronique
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supporting information
p. 13366 - 13369
(2015/11/09)
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